2-Amino-4-phenylthiazole

Base Information

• Chemical Name: 2-Amino-4-phenylthiazole
• CAS No.: 2010-06-2
• Molecular Formula: C9H8N2S
• Molecular Weight: 176.242
• Hs Code.: 29341000
• European Community (EC) Number: 217-926-8
• NSC Number: 2528
• UNII: WF2822RIUS
• DSSTox Substance ID: DTXSID4043804
• Nikkaji Number: J37.311G
• Wikidata: Q27292601
• ChEMBL ID: CHEMBL175296
• Mol file: 2010-06-2.mol

Synonyms:2-amino-4-phenylthiazole;phenthiazamine;phenthiazamine hydrochloride;phenthiazamine monohydrobromide;phenthiazamine monohydrochloride;phenthiazamine monomesylate;phenthiazamine monoperchlorate

Chemical Property of 2-Amino-4-phenylthiazole

Chemical Property:

• Vapor Pressure: 1.8E-05mmHg at 25°C
• Melting Point: 149-153 °C(lit.)
• Boiling Point: 363.4 °C at 760 mmHg
• PKA: 4.33±0.10(Predicted)
• Flash Point: 173.6 °C
• PSA: 67.15000
• Density: 1.261g/cm³
• LogP: 2.97350
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 176.04081944
• Heavy Atom Count: 12
• Complexity: 146

Purity/Quality:

99% ^*data from raw suppliers

4-Phenyl-2-thiazolamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn; Xi
• Hazard Codes: Xn,Xi,T
• Statements: 22-37/38-41-25
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CSC(=N2)N
• General Description: 2-Amino-4-phenylthiazole is a versatile intermediate in organic synthesis, particularly for constructing heterocyclic compounds such as thiazole-based carboximidamides and 2-aminothiazole derivatives. It can be synthesized via methods like the Hantzsch cyclization using phenacyl bromide and thiourea, or through catalytic systems involving Fe₃O₄ nanoparticles, N-halo reagents, or supported ionic liquids. Its applications include the preparation of polyaromatic carboximidamides inspired by marine alkaloids, highlighting its utility in medicinal and materials chemistry. Efficient synthetic protocols emphasize greener conditions, high yields, and catalyst reusability.

Technology Process of 2-Amino-4-phenylthiazole

There total 70 articles about 2-Amino-4-phenylthiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.3%

thiocarboxamide (115-08-2) + α-bromoacetophenone (70-11-1) → 2-Amino-4-phenylthiazole (2010-06-2)

Guidance literature:

In isopropyl alcohol; at 25 ℃; for 3h;

Reference yield: 97.0%

thiourea (17356-08-0) + acetophenone (98-86-2) → 2-Amino-4-phenylthiazole (2010-06-2)

Guidance literature:

With N-iodo-succinimide; In ethanol; at 20 ℃; for 1h; Reagent/catalyst; Solvent;

DOI:10.1016/j.molstruc.2017.05.004

Reference yield: 97.0%

1-chloroacetophenone (532-27-4,108321-66-0,164322-25-2) + thiourea (17356-08-0) → 2-Amino-4-phenylthiazole (2010-06-2)

Guidance literature:

In ethanol; at 140 ℃; for 0.1h; Temperature; Time; Microwave irradiation;

DOI:10.1021/op700187w

upstream raw materials:

ethanol

2-diazo-acetophenone

thiourea

acetophenone

Downstream raw materials:

N-(4-phenyl-thiazol-2-yl)-succinimide

nicotinic acid-(4-phenyl-thiazol-2-ylamide)

N-2-isonicotinoyl-4-phenyl-thiazol-2-amine

7-[(4-phenyl-thiazol-2-ylamino)-methyl]-quinolin-8-ol

Refernces

Design and synthesis of thiazole derivatives as potent FabH inhibitors with antibacterial activity

10.1016/j.ejmech.2013.11.020

The research focuses on the design and synthesis of thiazole derivatives as potent FabH inhibitors with antibacterial activity. The study aimed to develop new antibacterial agents by targeting the fatty acid biosynthetic pathway, specifically the enzyme FabH. Two series of compounds, A (4ae4g) and B (5ae5g), were synthesized by forming an amine bond between aromatic acids and 4-phenylthiazol-2-amine or 4-(4-bromophenyl)thiazol-2-amine. These thiazole derivatives were evaluated for their antibacterial activity against four bacterial strains using the MTT assay, with minimum inhibitory concentration (MIC) values ranging from 1.56 mg/mL to 100 mg/mL. The compounds also showed FabH inhibition ability with IC50 values ranging from 5.8 mM to 48.1 mM. The research involved the synthesis of key intermediates, the formation of amide bonds, and the evaluation of antibacterial activity. Docking simulations and 3D-QSAR studies were conducted to understand the binding mode and structure-activity relationships. The analyses included elemental analysis, NMR, MS, and enzyme assays to determine the IC50 values. The experiments used various reagents, such as aluminum chloride, bromine, thiourea, and acetyl chloride, and involved techniques like thin-layer chromatography, melting point determination, and ESI mass spectrometry. The study concluded that compound 5f exhibited the best antibacterial and E. coli FabH inhibitory activity, suggesting its potential as an antibacterial agent.